Nitric Acid → HCID 10118774, compound

HRID 1247709Notes

Reaction equation

HRID 1247709 reaction equation
N([O-])=O.[Na+].[N+]([O-])(O)=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)([OH:36])[C:29]4[N:33]([CH3:34])[C:32](S)=[N:31][N:30]=4)[CH:26]=3)[N:21]([CH3:44])[C:20](=[O:45])[CH:19]=2)[CH:13]=[CH:14][CH:15]=1>O.C1COCC1>[Cl:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)([OH:36])[C:29]4[N:33]([CH3:34])[CH:32]=[N:31][N:30]=4)[CH:26]=3)[N:21]([CH3:44])[C:20](=[O:45])[CH:19]=2)[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 23668193Sodium NitriteHCID 178481708HCID 178481708, compound

Product 1

HCID 10118774HCID 10118774, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium nitrite (0.0007 mol) was added at 0° C. to a mixture of nitric acid (0.0007 mol) in water (1 ml). A solution of 4-[2-(3-chlorophenyl)ethyl]-6-[(4-chlorophenyl)hydroxy(5-mercapto-4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinone, obtained in Example B19 (0.0007 mol) in THF (3 ml) was added dropwise (very exothermic reaction). The mixture was stirred at room temperature for 30 minutes, poured out into ice water and extracted with DCM. The organic layer was separated, washed with K2CO3 10%, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over kromasyl (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.4; 5 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.25 g) was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.12 g (32%) of 4-[2-(3-chlorophenyl)ethyl]-6-[(4-chlorophenyl)hydroxy(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-1-methyl-2(1H)-quinolinone, melting point 200° C.

Workup

  1. additionwas added dropwise (
  2. customvery exothermic reaction)
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. washwashed with K2CO3 10%
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over kromasyl (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.4; 5 μm)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue (0.25 g) was crystallized from CH3CN
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-a5eac67c4e054eefa664e3d1c4eb7885
Source dataset
uspto-grants-2006_10
Patent number
US07129356B2

Reaction notes

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